Chiral Brønsted Acid Catalyzed Enantioselective aza-Friedel–Crafts Reaction of Cyclic α-Diaryl <i>N</i>-Acyl Imines with Indoles

Glavač, Danijel; Zheng, Chao; Dokli, Irena; You, Shu‐Li; Gredičak, Matija

doi:10.1021/acs.joc.7b01420

Cited by 58 publications

(20 citation statements)

References 46 publications

(49 reference statements)

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“…Among the established methods for the synthesis of chiral 3,3‐disubstituted isoindolinones, a particularly straightforward approach is the catalytic enantioselective addition of nucleophilic partners to cyclic N ‐carbonyl ketimines, which were generated in situ by dehydration of 3‐hydroxyisoindolinones (Scheme b). Followed this concept, the research groups of Zhou and Gredičak reported the asymmetric addition of indoles to 3‐hydroxyisoindolinone‐derived cyclic N‐ carbonyl ketimines. Hayashi and co‐workers developed a rhodium‐catalyzed asymmetric arylation of 3‐hydroxyisoindolinones by employing arylboroxines as nucleophiles.…”

Section: Methodsmentioning

confidence: 99%

Enantioselective Addition of Enamides to Cyclic Ketimines: Access to Chiral 3,3‐Disubstituted Isoindolin‐1‐Ones

Feng

Shen

et al. 2019

Adv Synth Catal

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An enantioselective addition of enamides to cyclic ketimines generated in situ from 3hydroxyisoindolin-1-ones was developed. This reaction takes advantage of readily available substrates, mild reaction conditions, as well as enlarged reaction generality, affording chiral 3,3-disubstituted isoindolin-1-ones with a quaternary stereogenic center in high yields (up to 98%) and enantioselectivities (up to 99% ee). Scheme 1. Synthesis of chiral 3,3-disubstituted isoindolin-1ones. Scheme 2. Substrate scope with respect to 3-hydroxyisoindolinones. [Reaction conditions: 1 a-q (0.2 mmol), 2 a (0.5 mmol), (S)-5 (0.01 mmol) in CH 2 Cl 2 (2 mL) at 25°C.] Scheme 3. Substrate scope with respect to N-acetyl enamines. [Reaction conditions: 1 a (0.2 mmol), 2 a'-o' (0.5 mmol), (S)-5 (0.01 mmol) in CH 2 Cl 2 (2 mL) at 25°C.] Scheme 4. Synthetic transformations of the products. Scheme 5. Control experiments.Scheme 6. Proposed mechanism and transition state model.

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Section: Methodsmentioning

confidence: 99%

Enantioselective Addition of Enamides to Cyclic Ketimines: Access to Chiral 3,3‐Disubstituted Isoindolin‐1‐Ones

Feng

Shen

et al. 2019

Adv Synth Catal

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“…You group and Gredicak group developed chiral SPAs‐catalyzed enantioselective aza ‐Friedel−Crafts reaction of cyclic diaryl N ‐acyl imines with indoles (Scheme 19). [ 23 ] Asymmetric addition of indoles to cyclic N ‐acyl imines, which are generated in situ from 3‐hydroxyisoindolinones, enabled by catalyst ( S ) ‐ SPA 11 afforded α‐tetrasubstituted (3‐indolyl)‐(diaryl)methanamines in excellent yields (up to 98%) and enantioselectivities (up to >98% ee).…”

Section: Asymmetric Organocatalysismentioning

confidence: 99%

Chiral Spirocyclic Phosphoric Acids and Their Growing Applications

et al. 2021

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What is the most favorite and original chemistry developed in your research group? Developing SPINOL-phosphoric acids (SPAs), TM-SPINOL-phosphoric acids (SPAs 2.0) and PCP-derived planar chiral phosphoric acids (PPAs) for asymmetric catalysis. What is the most important personality for scientific research? Curiosity, optimism, self-confidence and persistence. What's your hobbies? What's your favorite book(s)? I enjoy cooking. My favorite book is Journey to the West. Who influences you mostly in your life? My mother. What is your favorite journal(s)? The journals publishing the original and systematic work of synthetic chemistry. Could you please give us some advices on improving Chinese Journal of Chemistry? Fast review, fast publication, fast promotion via new media.

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“…(scheme 11) β-carbazoline compounds are important pharmacological active components in indole alkaloids, which widely exist in natural products and drugs [44,[52][53][54][55][56][57]. In 2017, Lin Xufeng's group further explored the aza Friedel Crafts reaction of indole and 1-trifluoromethyl-3,4-dihydro-β-carboline catalyzed by SPA [58], and obtained high yield (81%) and corresponding selectivity ( In 2017, the Gredicak Matija's group provided an aza Friedel Crafts reaction for the preparation of chiral αtetrasubstituted (3-indolyl) -(diaryl) methylamines [59]. Before that, there was no synthesis method with high corresponding selectivity [60][61].…”

Section: Friedel-crafts Reactionmentioning

confidence: 99%

Applications of chiral spirocyclic phosphoric acid in the synthesis of natural products

Yang

2021

E3S Web Conf.

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With a 10 years development, chiral spirocyclic phosphoric acids (SPAs) have attracted a substantial amount of attention from the synthetic organic chemistry community. This kind of small molecule organic catalysts has some advantages like easy to obtain, no transition metal and wide application range. Because of avoiding the use of toxic substances which are limited in the process of drug synthesis, a large number of studies pay attention to the key structures (such as indole, carbozole.) containing pharmacological active components in natural products. And most of them get a excellent result in yields (more than 80% yield) and enantioselectivities (more than 90% ee). These studies can provide new pathways to nature products.

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Chiral Brønsted Acid Catalyzed Enantioselective aza-Friedel–Crafts Reaction of Cyclic α-Diaryl N-Acyl Imines with Indoles

Cited by 58 publications

References 46 publications

Enantioselective Addition of Enamides to Cyclic Ketimines: Access to Chiral 3,3‐Disubstituted Isoindolin‐1‐Ones

Enantioselective Addition of Enamides to Cyclic Ketimines: Access to Chiral 3,3‐Disubstituted Isoindolin‐1‐Ones

Chiral Spirocyclic Phosphoric Acids and Their Growing Applications

Applications of chiral spirocyclic phosphoric acid in the synthesis of natural products

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